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Exploiting photocatalysed reactions under continuous flow conditions: cation-radical Diels-Alder reactions mediated by porphyrinoids

Grant number: 16/17818-4
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): November 01, 2016
Effective date (End): October 31, 2017
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Kleber Thiago de Oliveira
Grantee:Laís Cavalheiro Seneme
Home Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

Herein, studies about cation-radical Diels-Alder reaction will be performed using different electron-rich diene and dienophiles under continuous flow photocatalytic conditions. Essentially, metal or free-base porphyrin derivatives will be studied as photocatalyst excited by visible light, and an additional class of photocatalysts could be used if adequate.Among the electron-rich dienophiles which were selected we highlight anethole, vinylic ethers and vinylic thioethers. Dienes such cyclopentadiene, furan, isoperene and some natural dienes will also be tested comprising a-phelandrene and perilaldehyde derivatives.In addition, we intend to evaluate the mentioned photosensitizers as SET (single electron transfer photocatalysts in order to generate dienophiles radical-cations which will be reacted with electron-rich dienes. With the purpose of comparison, batch and continuous flow conditions will be evaluated by using white LED source. This subproject is completely inserted into the research under development at the LQBO-UFSCar in which we started in 2015 with the purpose of using porphyrinoids as photocatalysts in many reactions performed under continuous flow conditions (FAPESP founding 2015/21110-4).